VP of Revenue

Jobtailor; San Diego (CA); Hybrid; USD 180,000 - 280,000; Full time

Job summary

Jobtailor is seeking an enterprise sales leader to own and scale the full revenue function in a hybrid San Diego setting. You will build the GTM strategy, oversee Territory Directors, and lead SDR/BDR programs to drive pipeline into an Enterprise GTM organization.

The role requires 8+ years in B2B SaaS sales with at least 3+ years in leadership, healthcare/behavioral health experience, and a strong track record in scaling multi-territory teams.

Qualifications

• 8+ years in B2B SaaS sales.
• 3+ years in a sales leadership role owning a full revenue function.
• Experience selling into healthcare or behavioral health.
• Experience building and scaling a sales team, including hiring and ramping multiple reps.
• Ownership of pipeline generation in partnership with SDR/BDR functions.
• Strong command of CRM systems such as HubSpot or Salesforce.
• Knowledge of sales forecasting methodology.
• Experience designing sales compensation plans, territories, and quotas.
• Excellent executive communication with a CEO/board/investors.

Responsibilities

• Own full revenue funnel from pipeline generation through closed-won.
• Build and execute go-to-market strategy for scalable enterprise sales.
• Lead and scale Territory Director team as territories expand.
• Hire and onboard Territory Directors.
• Build and lead SDR/BDR function and pipeline generation targets.
• Own pipeline management and forecasting.
• Implement CRM discipline and executive reporting.
• Partner with Marketing on enterprise healthcare/behavioral health messaging.
• Design end-to-end sales process from qualification to close.
• Set pricing and packaging strategy with executive team.
• Partner with Customer Success on handoff, onboarding, expansion, renewals.
• Represent Clinically AI at industry events and with enterprise prospects.
• Build sales operations foundations including compensation, territory design, and quotas.
• Report to the CEO and collaborate on company-wide revenue strategy.

Skills

B2B SaaS sales leadership

Pipeline Management

Sales Compensation Design

CRM Systems Proficiency

Healthcare Sales Experience

Tools

HubSpot

Salesforce

Job description

• Own the full revenue funnel from pipeline generation through closed-won
• Build and execute the go-to-market strategy to create a scalable, repeatable enterprise sales engine
• Lead and scale the Territory Director team as the company expands from 4+ territories into an Enterprise GTM organization
• Hire and onboard new Territory Directors
• Build and lead the SDR/BDR function, including pipeline generation targets, outbound strategy, and SDR-to-Territory Director handoff
• Own pipeline management and forecasting
• Implement CRM discipline, deal stages, and executive reporting
• Partner with Marketing on lead generation, campaign strategy, and messaging for enterprise healthcare and behavioral health buyers
• Design and own the end-to-end sales process, including qualification, discovery, demo, proposal, negotiation, and close
• Set pricing and packaging strategy with the executive team
• Partner with Customer Success and Implementation on closed-won handoff, onboarding, expansion, and renewal opportunities
• Represent Clinically AI at industry events, conferences, and with strategic enterprise prospects
• Build sales operations foundations including compensation plans, territory design, and quota setting
• Report directly to the CEO
• Partner with the executive team on company-wide revenue strategy and board-level reporting

Requirements

• 8+ years in B2B SaaS sales
• At least 3+ years in a sales leadership role (VP, Head of Sales, Lead or Sales Manager or similar) owning a full revenue function
• Direct experience selling into healthcare, behavioral health, or another regulated, complex-buyer industry
• Track record of building and scaling a sales team, including hiring, ramping, and managing multiple reps or territory leads
• Experience owning pipeline generation in partnership with, or direct ownership of, an SDR/BDR function
• Strong command of CRM systems such as HubSpot, Salesforce, or similar
• Knowledge of sales forecasting methodology
• Experience designing sales compensation plans, territories, and quotas
• Excellent executive communication skills, including presenting revenue strategy and forecasts to a CEO, board, or investors
• AI Native operator with demonstrated successes and learnings
• High ownership mindset and comfort operating with significant autonomy in an early-stage environment
• Experience selling AI-enabled or clinical software into healthcare or behavioral health organizations specifically (preferred)
• Experience at a high-growth startup where revenue scaled quickly, such as Series A–C stage (preferred)
• Prior experience building a multi-territory field sales team from an initial handful of reps (preferred)
• Experience partnering closely with Customer Success or Implementation on expansion and retention motions (preferred)
• Must be legally authorized to work in the United States
• Willingness to undergo a background check in accordance with local law/regulations
• Comfortable working in a hybrid setting
• Currently located in San Diego, CA or open to relocation

Core Competencies

Demonstrates expertise in B2B SaaS sales leadership, with a strong focus on pipeline management, sales strategy execution, and team building within the healthcare and behavioral health sectors. Proven ability to drive revenue growth through effective sales processes and collaboration with cross-functional teams.

Highest-signal resume keywords

• B2B SaaS Sales Leadership
• Pipeline Management
• Sales Compensation Design
• CRM Systems Proficiency
• Healthcare Sales Experience

ATS Optimization Keywords

Hard Skills

• Sales Forecasting Methodology
• Sales Process Design
• Pipeline Generation
• Territory Management
• Sales Team Scaling

Soft Skills

• Executive Communication
• High Ownership Mindset
• Autonomy in Early-Stage Environments

Industry Keywords

• Healthcare
• Behavioral Health
• AI-Enabled Software
• Regulated Industry
• B2B Sales

Tools & Technologies

• HubSpot
• Salesforce